(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol | 159751-72-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol
• 英文别名: (3S,4R,5S,8S)-8-methoxy-3,5-dimethyl-8-(3-phenylmethoxyphenyl)oct-1-yn-4-ol
• CAS: 159751-72-1
• 化学式: C₂₄H₃₀O₃
• 分子量: 366.5
• InChiKey: YBGVWIQJPJRNNR-WJNSRDFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol 在 N-氯代丁二酰亚胺 、 正丁基锂 、 pyridine-SO3 complex 、 水 、 silver nitrate 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 生成 (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarbaldehyde
  参考文献：
  名称：

  Synthetic study on oscillatoxin D: Construction of the C1–C26 spiroether segment by intramolecular aldol condensation and Michael-type addition

  摘要：

  The C-1-C-7 segment (10) and the C-8-C-21 segment (14) of oscillatoxin D have been synthesized efficiently. The acyclic compound obtained by coupling of these two segments, has been converted int the C-1-C-26 spiroether (18) possessing the same stereogenic centers of oscillatoxin D. The construction of the spiroether has been achieved by intramolecular aldol condensation and Michael-type addition as key steps.

  DOI：

  10.1016/s0040-4039(00)73355-7
• 作为产物：
  描述：

  {(4R,5R,6R)-6-[(1S,4S)-4-(3-Benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-methanol 在 四氯化碳 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol
  参考文献：
  名称：

  Synthetic study on oscillatoxin D: Construction of the C1–C26 spiroether segment by intramolecular aldol condensation and Michael-type addition

  摘要：

  The C-1-C-7 segment (10) and the C-8-C-21 segment (14) of oscillatoxin D have been synthesized efficiently. The acyclic compound obtained by coupling of these two segments, has been converted int the C-1-C-26 spiroether (18) possessing the same stereogenic centers of oscillatoxin D. The construction of the spiroether has been achieved by intramolecular aldol condensation and Michael-type addition as key steps.

  DOI：

  10.1016/s0040-4039(00)73355-7

文献信息

• Synthetic study on oscillatoxin D: Construction of the C1–C26 spiroether segment by intramolecular aldol condensation and Michael-type addition
  作者：Hiroaki Toshima、Takashi Goto、Akitami Ichihara

  DOI：10.1016/s0040-4039(00)73355-7

  日期：1994.6

  The C-1-C-7 segment (10) and the C-8-C-21 segment (14) of oscillatoxin D have been synthesized efficiently. The acyclic compound obtained by coupling of these two segments, has been converted int the C-1-C-26 spiroether (18) possessing the same stereogenic centers of oscillatoxin D. The construction of the spiroether has been achieved by intramolecular aldol condensation and Michael-type addition as key steps.